Does Looking Fly on Your Run Make You Fly Through Your Run?

Does Looking Fly on Your Run Make You Fly Through Your Run?

Nov 03, 2026


I ran my first marathon this month in Newport, Rhode Island, and I’m not sure which was prettier: the seaside views or me dashing over 26 miles in my Bandit shorts and butter-yellow Cleo Camp tee. The shorts are an expected stylistic choice, worn by many of my fellow racers, compressed so whoever wears them forgets they’re there, and decorated with pockets to fit GUs and Honey Stinger waffles to recharge. However, I’d bet money on the guess that I am the first person to run a marathon in a Cleo tee. Hell, I’d guess I’m the first girl to run any road race in a Cleo tee.

The top, most notably worn by stars like Audrey Hobert, Phoebe Bridgers, and Kendall Jenner, has also quickly become a cult-classic staple for girl-next-door types everywhere. The independent brand, created in Los Angeles, often features women working in its signature reversible tee to market its product on social media. Even with my knowledge that line cooks, servers, and musicians alike are donning the damn thing, I still believe I’m helping pioneer its role in athleticwear.

Though this was my first full marathon, I’ve been running for many years. In all that time, I have also been making some choices in garb that others may consider wack. I’ve long held the belief that the number of fingers on one hand matches the number of Brandy Melville items I wouldn’t consider running-appropriate. I remember PR’ing my 5K on a whim one day last winter in a pointelle long-sleeve from the scorned brand. Its high cotton content feels nice; the natural form-fit its garments give my 5’11” self is what I’d conversely be paying a proper workout-wear brand to provide me.

Another of my personal favorite activewear brands is Tankair, which, by both its bold price point and polyester-spandex blends, could be confused with Lululemon. Their few differences are found in the girls who wear them and what they do in them. I sported my Studio Tank for another PR, a 5:38 mile I crushed this May.

Part of me knows my relationship to running clothing is an external expression of my need-to-be-different syndrome. I’ve been this way since my days of showing up to my upstate New York public high school in sheer Cop Copine tops, duct taped nipples beneath. Even if it looks bad, I have a carnal drive to somehow stand out or subvert. Like everything in my life, I see style with a lens of transness.

I also run with my trans identity in mind. I’m addicted to running because daily morning miles might be the one chance I have in a day to clear my head of the hatred, ignorance and dehumanization my community faces seemingly only more and more as time passes. Though I don’t particularly look to affirm myself with my running clothes, I spend plenty of time on the road in matching Beyond or Aritzia sets, which do wind up feeling good mentally. I own two Lulu BBL jackets for when I run in the chill of my hometown, and wind up fitting in with the suburban moms when I stop into the grocery store for water post-workout. Conversely, I often run in a teeny, cropped white tee that says “GULP!” I only bought it because Ethel Cain wore it a few years back, and because the brand that makes it is trans-owned. I take my transness and its resulting style with me everywhere.

Not everyone’s silly running style will look identical toor come with the same subconscious motivations as mine though.

In my orbit, there is a wise woman whom I look to for running and life inspiration. A blonde-locked baddie who wears her affinity for Hanro basics-suited Nicole Kidman in Eyes Wide Shut and eBay-sourced hair clips the same way she does her love for running in some fly yet on-the-fringe outfits. She provided inspiration for my marathon outfit choice when she posted a pre-run selfie a few weeks back in her own Cleo tee, telepathically telling me that this was the top I knew deep down I needed to wear on race day. Allegra Samsen is running her own first marathon in New York City this November.

“I can wear a Cleo tee for a short run, but for anything longer, I need to go sleeveless,” Samsen says. She played sports in high school but took a break while studying at our coincidentally shared Los Angeles alma mater.

“I joined a co-ed soccer team two years ago. I was curious again about leisurely hobbies outside of spending money. I got addicted and felt so speedy. I would rip my knees on astroturf, then leave carrying my Paloma Wool tote. These moments are ‘Allegra-doms.’ She’s the Man bullshit mixed with Beckham swagger.”

Shortly after starting soccer scrimmaging, she decided to work on her stamina.

“I was walking on the West Side Highway. I remember the exact song I was listening to and how it made me start running. That was October 2024. I ran a half-marathon in December 2024.”

As with many of us, sports styling was a learning curve for Samsen.

“I used to run in vintage Prada Sport, but would notice how scratchy it would become after a few miles. In the humidity, I love Frankie’s Bikini tops.”

She views her running attire as formulaic. Her closet’s contents are the numerals.

“It’s math that I love doing. I don’t always get the right answer, and that’s because there may never be one. The equation is the run itself, which makes me never want to stop.”

While getting dressed, she accounts for the proper fueling that comes with distance running.

“Sometimes style is dependent on what I need on my run. Pocketed shorts for fuel and a water bottle. It’s easy to forget how unique it is to be running those high-mileage weeks. A lot of marathon training isn’t pretty. Running more requires lots of compromise.”

I bring up my affinity for Brandy, which she leaps to agree with.

“I cross-train with pole dance and wear Brandy boyshort boxers.”

For Samsen, even footwear and accessories have been an experiment.

“Some of my first serious runs were in Salomon hiking sneakers. I didn’t know about the hyper-nicheness of certain brands. I run in a Stüssy cadet cap a lot. It’s functional. And a cool embellishment.”

Samsen speaks about how others among her social media followers are quite curious about her running habits. She just wants to make sure everyone stays safe.

“I love this sport for all its weirdness and joy. But I’ve let it destroy me and my clothing. In a beautiful way. There are sports bras we’ll never get rid of, shoes that have visibly decayed, that we still want to wear. Let that love and destruction reveal itself. It’s a reflection of what we’ve done.”

As for what to wear? She thinks it’s simultaneously the simplest and most complex set of choices.

“My advice is throwing out the textbook. Run, then your mind will decide on the clothing that matches what you feel while doing it. The style reflects the action, which yields self-expression. Learn your language and speak it.”

I agree. Don’t let the decision between that free T-shirt from the turkey trot you ran in middle school and the cutest new Cleo colorway plague you. Wear whichever feels good and gives you the opportunity to fuel good. Let the run be the hard part. For me, a Cle Cle tee and some Bandit booty shorts hit a sweet, mathematical spot for 26.2. What will the proper pieces be for you?

Photography courtesy of Andie and Allegra